A Completely Diastereoselective Electrophilic Fluorination of a Chiral, Noncarbohydrate Sugar Ring Precursor: Application to the Synthesis of Several Novel 2'- …

JJ McAtee, RF Schinazi, DC Liotta

Index: Jeffrey McAtee; Schinazi, Raymond F.; Liotta, Dennis C. Journal of Organic Chemistry, 1998 , vol. 63, # 7 p. 2161 - 2167

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Citation Number: 74

Abstract

A new and completely diastereoselective method for the introduction of fluorine into a noncarbohydrate sugar ring precursor has been developed. The use of N- fluorodibenzenesulfonimide (5) for the electrophilic fluorination of chiral lactone 4, which is derived from l-glutamic acid, yields the key intermediate 6. This is transformed into an anomeric acetate 8 and is used for the synthesis of a number of novel α-2'- ...